Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
  • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
  • D06P1/642—Compounds containing nitrogen
  • D06P1/6426—Heterocyclic compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
  • C07D251/40—Nitrogen atoms
  • C07D251/48—Two nitrogen atoms
  • C07D251/50—Two nitrogen atoms with a halogen atom attached to the third ring carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
  • C07D251/40—Nitrogen atoms
  • C07D251/54—Three nitrogen atoms
  • C07D251/70—Other substituted melamines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
  • C07F9/02—Phosphorus compounds
  • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
  • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
  • C07F9/6521—Six-membered rings
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
  • D06M13/35—Heterocyclic compounds
  • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
  • D06M13/358—Triazines
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
  • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre

Definitions

• the invention is in the technical field of water-soluble, polyfunctional fiber-reactive triazine compounds which have fiber-refining properties.
• a triazine compound of this type is known from Example 1 of U.S. Patent 3,278,253.
• the substituents in A and B can be in any position of the aromatic nucleus.
• R is preferably a group of the general formula (2).
• groups Y and Z the vinyl and in particular the ⁇ -sulfatoethyl groups are preferred.
• R 1 and R 2 are both identical and each represents a hydrogen atom, a methyl group or an ethyl group, furthermore in particular those in which X is a chlorine atom.
• Preferred compounds of the general formula (1) are furthermore those in which the formula members A and B, the same or different from one another, each represents the phenylene radical which may be substituted by 1 or 2 substituents selected from the group consisting of 1 chlorine atom, 2 methoxy groups, 1 methyl group and 1 sulfo group.
• the present invention further relates to a process for the preparation of the compounds of the general formula (1), which is characterized in that cyanuric chloride in equimolar or approximately equimolar amounts of an amino compound of the general formula (4) and one
• the amines (4) and (5) are generally used in an excess of up to 10%, preferably up to 5%.
• the compounds of the formulas (4), (5) and (6) are reacted analogously per se and per se known and customary procedures for the reaction of aliphatic and aromatic amines, alcohols, phenols, mercaptans and thiophenols with cyanuric chloride, dichloro-s-triazine -Compounds or monochloro-s-triazine compounds (see, for example, Ullmanns Encyklopadie der industrial chemistry, 4th edition (1975), volume 9, p. 651).
• the preparation is carried out by reacting a di- or trichloro-s-triazine compound of the general formula (7) in which X is as defined above, with an amine of the above general formula (4) and an amine of the above general formula (5) in equimolar or approximately equimolar amounts, the reaction preferably being carried out in a two-stage reaction and the compound of the formula ( 7) first with the equimolar amount of an amine (4) or (5) to the compound of the general formula (8) in which X has the meaning given above and R ° for a radical of the general formula (9a) or (9b) with A , B, R 1 , R 2 , R and Y has the meaning given above, and then, preferably without intermediate isolation, the compound of the formula (8) with the amine of the general formula (5) or (4) to give the compound ( 1) implements. If the amino compounds of the general formulas (4) and (5) are identical, there is no need to convert the reaction components by adding the two amine
• the reaction of the cyanuric chloride or a dichloro- or monochloro-s-triazine compound of the general formula (8) can be carried out in an organic or aqueous-organic medium.
• Organic solvents are preferably acetone and Toluene. It is preferably carried out in an aqueous medium with the addition of acid-binding agents, such as alkali or alkaline earth carbonates, alkali or alkaline earth hydrogen carbonates or hydroxides or alkali acetates, the alkali and alkaline earth metals preferably being those of lithium, potassium, sodium and calcium;
• Acid-binding agents are also tertiary amines, such as pyridine, triethylamine or quinoline.
• the addition of small amounts of a commercially available auxiliary agent can also be expedient.
• the condensation reaction of the cyanuric chloride with an amine of the general formula (4) or (5) is usually carried out at a temperature between -10 ° C and + 40 ° C, preferably between -10 ° C and + 30 ° C, and at pH between 1.0 and 7.0, especially between 3.0 and 6.0.
• the reaction according to the invention of the compounds of the general formula (8) with the corresponding amino compound of the general formula (4) or (5) is generally carried out at a temperature between 0 and 70 ° C., in particular between 10 and 50 ° C., and at a pH between 2 and 9, in particular between 3 and 8, care being taken both when reacting the cyanuric chloride and the compounds of the formula (8) with such amines of the formula (4) and / or (5), that the pH does not exceed 7 if the amine contains a ß-thiosulfatoethylsulfonyl, ß-sulfatoethylsulfonyl or vinylsulfonyl group.
• Amino compounds of the general formula (4) which can serve as starting compounds for the preparation of the compounds (1) according to the invention are, for example, 4- ( ⁇ -sulfatoethylsulfonyl) -N-methyl-aniline, 4- ( ⁇ -sulfatoethylsulfonyl) -N- ( ⁇ -hydroxyethyl) aniline, 4- (ß-sulfatoethylsulfonyl) -N- (ß-cyanoethyl) aniline, N, N-bis- [ß- (ß'-chloroethylsulfonyl) ethyl] amine, 4- ( ⁇ -sulfatoethylsulfonyl) -phen ethylamine, 4- (ß-sulfatoethylsulfonyl) aniline, 3- (ß-sulfatoethylsulfonyl) aniline, 2- (ß-sulfatoethyl
• Amino compounds of the general formula (5) which can serve as starting compounds for the preparation of the compounds (1) according to the invention are, for example, 4- ( ⁇ - Sulfatoethylsulfonyl) -N-methyl-aniline, 4- (ß-sulfatoethylsulfonyl) -N- (ß-hydroxyethyl) aniline, 4- (ß-sulfatoethylsulfonyl) -N- (ß-cyanoethyl) aniline, N, N-bis - [ß- (ß'-chloroethylsulfonyl) ethyl] amine, 4- (ß-sulfatoethylsulfonyl) phenethylamine, 4- (ß-sulfatoethylsulfonyl) aniline, 3- (ß-sulfatoethylsulfonyl) aniline, 2- (ß-sulfatoethylsulf
• the compounds of general formula (1) prepared according to the invention can be separated and isolated from the synthesis solutions by methods generally known for fiber-reactive water-soluble compounds, for example by precipitation from the reaction medium by means of electrolytes, such as by means of sodium chloride or potassium chloride, or by evaporation of the reaction solution, for example by spray drying. Mother liquors that result from the reaction batches or solvents that are recovered can advantageously be recycled for further subsequent batches. In this way it is possible to isolate the water-soluble compounds of the formula (1), which are obtainable per se in high yield, with only little or no wastewater pollution by inorganic salts in effectively high yields.
• the new compounds of the general formula (1) serve to modify and improve the physical and dyeing properties of materials made from natural and / or synthetic polyamide fibers, such as wool, polyamide-6, polyamide-6,6 and polyamide-11, and / or polyurethane fibers as well as a valuable aid in dyeing processes for such materials. For example, they improve the levelness of polyamide dyeings if they are allowed to act on the natural and / or synthetic polyamide fiber before the actual dyeing process or together with the dye during the dyeing process. In the same way, it is possible, for example, to improve the wet tensile strength of wool by treatment with the new compounds of the formula (1).
• the fiber loss which usually occurs when dyeing wool at boiling temperature (by hydrolysis) can also be reduced with the aid of the new compounds of the formula (1), by adding the wool fabric or the wool flake before or during the dyeing process together with the dye, for example an acid dye or a reactive dye, with a compound of the formula (1), dissolved in a liquor or treated in the dye liquor itself.
• the action of the compounds of the general formula (1) on these fiber materials can be carried out analogously to process conditions and procedures as are customary and known for dyeing these fiber materials by means of fiber-reactive dyes (see, for example, page 15, lines 27 ff ., to page 16, line 9, and page 16, line 23 ff., to page 17, line 23, German Offenlegungsschrift No. 3 132 917).
• Parts by weight relate to parts by volume such as kilograms to liters.
• An aqueous solution with a pH of 4.5 of 562 parts of 4- ( ⁇ -sulfatoethylsulfonyl) aniline in 2000 parts of water is prepared using about 100 parts of sodium carbonate; 0.5 part of a commercially available dispersing agent is added and then 184 parts of cyanuric chloride in solid form are added at a temperature between 15 and 20 ° C. with stirring. While maintaining the specified pH value and the specified temperature range, the batch is stirred for a further two hours, then heated to 45 to 50 ° C. and at a pH value of 4.5 (which is maintained by means of sodium carbonate) for a further four hours and at this temperature Temperature continued to complete the condensation reaction.
• the batch is heated to 60 ° C. and water is added until this product is completely dissolved.
• the mixture is then filtered and the filtrate is spray-dried or evaporated.
• a white-gray powder which, in addition to electrolyte salts (such as sodium chloride), 86% (corresponding to a yield of 99.1% of theory) of the compound of the formula contains.
• electrolyte salts such as sodium chloride
• 86% corresponding to a yield of 99.1% of theory
• the melting point of the divinyl derivative can be used for characterization.
• the compound according to the invention is converted with aqueous sodium hydroxide solution at room temperature into the corresponding insoluble di-vinyl sulfone compound which has a decomposition point of 180 ° C.
• the compound according to the invention improves, for example, the wet tensile strength of wool if wool is treated in an aqueous bath with the compound according to the invention dissolved therein (see also the later application example).
• the solution of the product according to the invention thus produced is filtered and the filtrate is spray-dried. 720 parts of a light gray powder are obtained which, in addition to electrolyte salts, 83% (corresponding to a yield of 97.7% of theory) of the compound of the formula contains.
• the compound according to the invention improves, for example, the wet tensile strength of wool when it is treated with the compound according to the invention in an aqueous bath, for example analogously to the later application example.
• Example 2 To prepare a compound according to the invention, the procedure of Example 2 is followed, except that in section b), in the second condensation reaction, 107 parts of N-methylaniline are used instead of the sulfanilic acid.
• a white-gray powder which is the compound of the formula according to the invention 80% corresponding to a yield of 96.6% of theory contains.
• the compound according to the invention improves, for example, the wet tensile strength of wool when it is treated with the compound according to the invention in an aqueous bath, for example analogously to the later application example.
• Example 2 To synthesize the vinylsulfonyl derivative according to the invention of the compound described in Example 2, the procedure of Example 2 is initially followed, but after filtering the synthesis batch, the pH of the filtrate is adjusted to a value at 20 ° C. using a 30% strength aqueous sodium hydroxide solution out of 10 and holds it for 15 minutes. After neutralizing the solution By means of concentrated aqueous hydrochloric acid and spray drying, the compound of the formula according to the invention is obtained in the form of a gray, electrolyte-containing powder in a yield of 87% of theory.
• the compound according to the invention improves, for example, the wet tensile strength of wool when it is treated with the compound according to the invention in an aqueous bath, for example analogously to the later application example.
• Example 2 To prepare a compound according to the invention, the procedure of Example 2 is followed, but in process step b), after the second condensation reaction, an additional 110 parts of diethanolamine are used and the third condensation reaction is carried out for three hours at 80 ° C. and a pH of 6. 0 through. After clarification of the synthesis batch and after spray drying of the filtrate, a slightly yellow colored electrolyte-containing powder with the compound of the formula according to the invention is obtained in a yield of 85% of theory.
• the compound according to the invention improves, for example, the wet tensile strength of wool when it is in an aqueous bath, for example analogously to the later Example of use, is treated with the compound of the invention.
• the compounds according to the invention described in the table examples can be prepared in a manner according to the invention, for example analogously to the methods described in the previous exemplary embodiments, with the components which can be seen from the table examples as starting compounds (the amino compound of the general formula A * -NH2 ', the amino compound of the general formula H 2 NB * and the cyanuric chloride or the dichloro-s-triazine compound).
• a woolen fabric 100 parts are introduced into a 40 ° C. aqueous bath which consists of 3000 parts of water, 3 parts of the sodium salt of the compound according to the invention described in Example 1, 0.15 part of an adduct of 12 moles of ethylene oxide and 1 mole of stearylamine, 2 parts Ammonium acetate and 2 parts of 60% aqueous acetic acid.
• the temperature is raised to the boiling temperature within 30 minutes and the wool is then further treated at 100 ° C. for 60 minutes. After the usual washing and finishing, this wool fabric shows a significantly better wet tensile strength than untreated wool.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Biochemistry (AREA)
• General Health & Medical Sciences (AREA)
• Molecular Biology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• General Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Coloring (AREA)

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• 1984
  • 1984-09-15 DE DE19843433983 patent/DE3433983A1/de not_active Withdrawn
• 1985
  • 1985-09-06 EP EP85111251A patent/EP0175225A3/fr not_active Withdrawn
  • 1985-09-12 FI FI853495A patent/FI853495A7/fi not_active Application Discontinuation
  • 1985-09-13 JP JP60201918A patent/JPS6173771A/ja active Pending

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